Metal coordination protocol for the synthesis of-2,3-dehydrosilybin and 19-O-demethyl-2,3-dehydrosilybin from silybin and their antitumor activities |
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| Authors: | Yong-ju Wen Zong-yuan Zhou Guo-lin Zhang Xiao-xia Lu |
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| Affiliation: | 1. Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China;2. Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Hainan 571127, China;3. University of Chinese Academy of Sciences, Beijing 100049, China;4. Chemistry and Biology Bioengneering College, Yichun University, Yichun 336000, China |
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| Abstract: | An efficient and practical method to access bioactive 2,3-dehydrosilybin and 19-O-demethyl-2,3-dehydrosilybin using naturally abundant flavonolignan silybin in the presence of metal salt as a chelating agent is described. The procedure presented here has several advantages including one-pot, synthetic ease, and products in high yields with no side reactions, and large-scale feasibility. The dehydrogenation and demethylation proceed smoothly via a one-pot process using the AlCl3/Pyridine system and I2 as the additive. Furthermore, 2,3-dehydrosilybin and 19-O-demethyl-2,3-dehydrosilybin can inhibit the expression of intracellular mature miRNA-21 with IC50 values of 4.46?μM and 8.25?μM, respectively, and show moderate anticancer activities against HeLa cell lines. |
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| Keywords: | Silybin 2,3-Dehydrosilybin Synthesis Metal chelating Antitumor |
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